This invention relates to novel sulfonylurea herbicidal compounds, agriculturally suitable compositions thereof and a method of using them to control the growth of undesired vegetation.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
The "sulfonylurea" herbicides are an extremely potent class of herbicides discovered within the last few years. A multitude of structural variations exist within this class of herbicides, but they generally consist of a sulfonylurea bridge, --SO.sub.2 NHCONH--, linking two aromatic or heteroaromatic rings.
U.S. Pat. No. 4,514,211 discloses herbicidal sulfonamides of formula ##STR1## wherein L is ##STR2## R.sub.6 is H, Cl, Br or C.sub.1 -C.sub.4 alkyl; R.sub.6 ' is H, CH.sub.3, Cl or Br; and
Q.sub.1 is O, S or SO.sub.2. PA1 R.sub.2 is H or C.sub.1 -C.sub.4 alkyl; and PA1 R.sub.5 is H or CH.sub.3. PA1 R.sub.1 is H, Cl, Br, NO.sub.2, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, CO.sub.2 R.sup.2, C(O)NR.sup.3 R.sup.4, SO.sub.2 R or SO.sub.2 NR.sup.6 R.sup.7. PA1 R.sub.1 is H, C.sub.1 -C.sub.4 alkyl, CO.sub.2 R.sub.6, C(O)NR.sub.7 R.sub.8, C(O)R.sub.10, SO.sub.2 R.sub.10, or SO.sub.2 NR.sub.11 R.sub.12 ; and PA1 R.sub.2 is H, C.sub.1 -C.sub.3 alkyl or SO.sub.2 C.sub.6 H.sub.5. PA1 R.sub.2 is H or CH.sub.3 ; and PA1 W is O, S, or NR.sub.3. PA1 W.sub.1 is O, S, SO or SO.sub.2 ; PA1 R.sub.1 is H or CH.sub.3 ; and PA1 R.sub.2 is H or C.sub.1 -C.sub.4 alkyl. PA1 R.sub.1 is H, CH.sub.3, Cl or F; PA1 R.sub.6 is H, Cl or F; PA1 R.sub.7 is H, Cl or F; and PA1 R.sub.8 is H, Cl or F. PA1 R.sub.1 is H, halogen, NO.sub.2, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl or C.sub.2 -C.sub.5 alkoxyalkoxy. PA1 A is an unsubstituted or substituted unsaturated bridge of 4 atoms, of the formula --CH.dbd.CH--Y--, wherein Y is a bridge member of 2 atoms which is selected from the series consisting of --NH--CO--, --NH--SO.sub.2 --, --S--CO--, --S--SO.sub.2 --, --O--CO-- or --O--SO.sub.2 --. PA1 E is a single bond, CH.sub.2 or O; PA1 R.sub.1 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, nitro, C.sub.1 -C.sub.3 alkoxy, SO.sub.2 NR.sub.a R.sub.b, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, CH.sub.2 CN, CN, CO.sub.2 R.sub.c, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 haloalkylthio, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 alkylthioalkyl, CH.sub.2 N.sub.3 or NR.sub.d R.sub.e ; PA1 R.sub.a is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 cyanoalkyl, methoxy or ethoxy; PA1 R.sub.b is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; or PA1 R.sub.a and R.sub.b may be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; PA1 R.sub.c is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 haloalkyl, C.sub.2 -C.sub.3 cyanoalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or C.sub.2 -C.sub.4 alkoxyalkyl; PA1 R.sub.d and R.sub.e are independently H or C.sub.1 -C.sub.2 alkyl; PA1 Q.sub.1 is S, SO.sub.2 or NR.sub.2 ; PA1 Q.sub.2 is O, S or NR.sub.2 ; PA1 Q.sub.3 is O, S or NR.sub.3 ; PA1 Q.sub.4 is O, S or NR.sub.4 ; PA1 n is 0, 1 or 2; PA1 R.sub.2 H, C.sub.1 -C.sub.3 alkyl, phenyl, benzyl, CH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 C.tbd.CH, CN, C.sub.1 -C.sub.3 haloalkyl, OH, OCH.sub.3 or OC.sub.2 H.sub.5 ; PA1 R.sub.3 is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.4 is H or CH.sub.3 ; PA1 R.sub.5 is H, halogen, CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, OCF.sub.2 H or halomethyl; PA1 R.sub.6 is C.sub.1 -C.sub.4 alkyl; ##STR13## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino or C.sub.3 -C.sub.5 cycloalkyl; PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, azido, cyano, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, ##STR14## NR.sub.d (C.sub.2 -C.sub.3 cyanoalkyl) of N(OCH.sub.3)CH.sub.3 ; m is 2 or 3; PA1 L.sub.1 and L.sub.2 are independently O or S; PA1 R.sub.f is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.g and R.sub.h are independently C.sub.1 -C.sub.3 alkyl; PA1 Z is CH or N; PA1 Z.sub.1 is CH or N; PA1 Y.sub.1 is O or CH.sub.2 ; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA1 X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ; PA1 Y.sub.2 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 Y.sub.3 is H or CH.sub.3 ; PA1 X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl; and PA1 Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl; PA1 (a) X is Cl, F, Br or I, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H; PA1 (b) when X or Y is C.sub.1 haloalkoxy, the Z is CH; PA1 (c) X.sub.4 and Y.sub.4 are not simultaneously Cl; PA1 (d) when W is S, then E is a single bond, R is H, A is A-1 and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or 1,3-dioxolan-2-yl; PA1 (e) when the total number of carbons of X and Y is greater than four, then the number of carbons of R.sub.1 must be less than or equal to two; PA1 (f) Q.sub.3 and Q.sub.4 are not simultaneously S; PA1 (g) when J is J-5, then Q.sub.3 is NR.sub.3 and Q.sub.4 is NR.sub.4 ; and PA1 (h) when n is O, then Q.sub.3 is NR.sub.3 and Q.sub.4 is NR.sub.4. PA1 (i) when R.sub.5 is other than H, then R is H, R.sub.1 is H, W is O, A is A-1 and E is a single bond. PA1 (j) when J is J-6 or J-7, then A is A-1. PA1 1. Compounds of Formula I where E is a single bond. PA1 2. Compounds of Formula I where E is CH.sub.2 and R.sub.5 is H. PA1 3. Compounds of Formula I where E is O and R.sub.5 is H. PA1 4. Compounds of Preferred 1 where PA1 5. Compounds of Preferred 4 where A is A-1. PA1 6. Compounds of Preferred 5 where J is J-1. PA1 7. Compounds of Preferred 5 where J is J-2. PA1 8. Compounds of Preferred 5 where J is J-3. PA1 9. Compounds of Preferred 5 where J is J-4. PA1 10. Compounds of Preferred 5 where J is J-5. PA1 11. Compounds of Preferred 5 where J is J-6. PA1 12. Compounds of Preferred 5 where J is J-7. PA1 13. Compounds of Preferred 6 where PA1 14. Compounds of Preferred 2 where PA1 15. Compounds of Preferred 3 where PA1 N[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-5-methoxy-1,2,3-benzothiadiaz ole-4-sulfonamide, m.p. 120.degree.-129.degree. C.(d); and PA1 N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-5-methoxy-1,2,3-be nzothiadiazole-4-sulfonamide, m.p. 176.degree.-178.degree. C. PA1 N-[[4-ethoxy-6-(methylamino)-1,3,5-triazin-2-yl]aminocarbonyl]-1-methyl-1H- benzotriazole-4-sulfonamide, m.p. 203.degree.-209.degree. C.
EP-A-107,979 discloses herbicidal sulfonamides of formula ##STR3## n is 0, 1 or 2; R is H or CH.sub.3 ;
U.S. Pat. No. 4,391,627 discloses herbicidal sulfonamides of formula ##STR4## where W is O or S; and
EP-A-70,698 discloses herbicidal sufonamides of formula ##STR5## where R is H, C.sub.1 -C.sub.4 alkyl, (CH.sub.2).sub.m CO.sub.2 R.sub.9, CH.sub.2 OC.sub.2 H.sub.5, SO.sub.2 R.sub.10, CHO, SO.sub.2 NR.sub.11 R.sub.12, CH.sub.2 N(CH).sub.3).sub.2 or CH.sub.2 OCH.sub.3 ;
EP-A-168,246 discloses herbicidal sulfonamides of formula ##STR6## R is H or C.sub.1 -C.sub.4 alkyl optionally substituted with 0-3 halogen atoms selected from 1-3 F, 1-2 Cl or 1 Br, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkoxy, CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 OCH.sub.3 or CH.sub.2 SCH.sub.3 ;
U.S. Pat. No. 4,502,882 discloses, in part, herbicidal sulfonamides of formula ##STR7## wherein W is O, S, SO or SO.sub.2 ;
U.S. Pat. No. 4,578,108 discloses, in part, herbicidal sulfonamides of formula ##STR8## Q is O, S(O).sub.n or NR.sub.3 ; n is 0, 1 or 2;
South African patent application No. 83/5165 (Swiss priority 7/16/82, published 1/16/84) discloses herbicidal sulfonamides of formula ##STR9## wherein A is an unsubstituted or substituted bridge of 3 or 4 atoms which contains 1 or 2 oxygen, sulfur or nitrogen atoms and, together with the linking carbon atom, forms a non-aromatic 5- or 6-membered heterocyclic ring system, with the proviso that two oxygen atoms are separated by at least one carbon atom and that oxygen and sulfur atoms are only linked to each other if the sulfur atom takes the form of the --SO-- or SO.sub.2 -- group, and R.sub.2 is hydrogen, halogen, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl or C.sub.2 -C.sub.5 alkoxyalkoxy; and
South African patent application No. 84/3522 (Swiss priority 5/11/83, published 11/11/84) discloses herbicidal sulfonamides of formula ##STR10## wherein R.sub.1 is H, halogen, NO.sub.2, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, CN, XR.sup.5, COXR.sup.6, CONR.sup.7 R.sup.8, SOR.sup.9 or SO.sub.2 R.sup.10 ; and
East German Pat. No. 134,184 (VEB Chemiekomb bitterfeld), published 2/14/79, discloses herbicidal sulphamoyl-2,1,3-benzothiadiazole derivatives of the formula ##STR11## wherein R.sup.20 and R.sup.30 are H or halogen; and R.sup.10 is carbamoyl N-substituted by a C.sub.1 -C.sub.4 aliphatic or C.sub.3 -C.sub.6 cycloaliphatic group.